


It’s a Happy Kind of Falling

by Insanefangirl



Category: Supernatural
Genre: Awkward Castiel, Established Dean Winchester/Castiel - Freeform, Lawyer Sam Winchester, M/M, Mechanic Dean, Meet the Family, Protective Sam Winchester, Sam Winchester Ships Castiel/Dean Winchester, Teacher Castiel
Language: English
Status: Completed
Published: 2020-11-15
Updated: 2020-11-15
Packaged: 2021-03-10 04:26:41
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,555
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27568237
Author URL: https://archiveofourown.org/users/Insanefangirl/pseuds/Insanefangirl
Summary: Sam is going to meet Dean’s new boyfriend. After his brother’s last relationship he can’t help be a little skeptical about this new guy
Relationships: Dean Winchester/Castiel, Sam Winchester & Dean Winchester
Comments: 13
Kudos: 305





	It’s a Happy Kind of Falling

Sam has met Dean’s significant others before. He hasn’t met a lot, but he has met the important ones; Cassie, from high school; Lisa, who Dean dated for two years and moved in with; Benny, who Dean had almost moved in with; and Michael, who Sam had not liked after seeing the guy eye his brother like a piece of meat, that relationship had lasted longer then it should have. 

Sam knows there had been others, Dean is rarely single. He knows Dean only introduces the ones who are really important to him. Sam, being the little brother he is, always thinks maybe this one will be the one. The one to make his brother happy forever.

So when Dean calls him and says he wants Sam to meet Cas, normally he would be excited. After Michael however, Benny had rubbed Sam the wrong way too, he was a little skeptical about getting too excited about this new guy. However Sam tries to stay optimistic and get details about this Cas. 

“I don’t know Sammy, he’s just awesome.” Sam can’t help his eye roll at his brother’s go to word choice. 

Before Sam can pry further a loud clatter is heard in the background and Dean says he’ll text him the details. 

Saturday night comes around and Sam heads to The Roadhouse. Run by people who were practically family, both brothers tend to use the restaurant as a public safe place for first dates and what nots. He sees Dean tucked into their usual booth. 

“Hey,” Sam sits across from him. “Cas not here yet?” 

“Nah, he just texted me. He’s running late from work.” Dean must have read something from Sam’s face because to quickly adds. “Which is super unlike him. He’s always on time if not five minutes early.” 

“Okay.” Sam goes for a nonchalant shrug but is glad Dean clarified. Michael would go weeks without contact and then come back as if nothing happened. It left Dean in a mess every time. 

Jo sets a beer in front of Sam and Dean asks for another for Cas. 

“Ah, so it’s the big night?” Jo smirks. “Boyfriend gets to meet the brother. He’s great, Sam, nothing to worry about, and Dean is head over heels.” 

“Am not.” Dean grumbles, his cheeks blooming red. Sam has already made the deduction that Dean likes this one. A lot. 

“If you say so.” Jo drawls as she walks away. 

“Oh, there he is.” Dean suddenly says. He waves a hand to get this Cas’ attention. 

Sam whirls around to see but a large gentleman is blocking his view. He cranes his neck but he can’t see anything. 

Finally a guy who must be the boyfriend comes into view. Cas is good looking. That was going to be a given, all of Dean’s significant others are good looking. 

Cas is maybe an inch shorter than Dean, with dark tousled sex hair, and blue eyes. His frame is mostly swallowed by an ill fitting trench coat over his dress pants and white dress shirt that has the top two buttons undone. From what Sam can tell though, he is fit. For the most part he looks mostly normal, the trench coat is a little weird since it isn’t that cold out, and the hair is borderline too much like sex hair. 

He doesn’t miss the way Dean scratches at the back of his neck as Cas approaches the booth. His brother is nervous and he wants this to go well. Okay, Sam’ll play nice. 

“My apologies for my lateness. I got held back by a student, then a coworker, and the traffic here was horrendous.” Cas is slightly out of breath as he speaks and slides next to Dean, placing a sweet kiss to his cheek. 

“No, problem. Nice to meet you, Cas.” Sam said sticking his hand out to be shaken. 

“Yes, nice to meet you, Sam.” Cas’ voice is deep and gravelly. He’s got a good handshake, and as progressive as Sam is, he still knows the value of a good handshake. 

“Student? Do you work at a school?”

“Yes, I work at the college teaching linguistic and cultural studies.” Sam’s eyes bug out. He can see Dean’s smirk at his expression. 

“Wow.” Is all that manages to come out of Sam’s mouth. Dean gives a snort earning him another glare. 

“Sam, Dean says you’re a lawyer? What classification is your occupation?” Cas takes a drink of his beer he had politely thanked Jo for. 

“Um, yeah, I’m in criminal law.” Sam says a little taken aback by the formal speech pattern. 

“Which is not as exciting as it sounds.” Dean helpfully adds. 

“Yeah and working with cars all day is super fascinating.” Sam jibes back. 

“Face it, Sam, you only chose criminal law because of your serial killer fetish.” 

“I think Dean’s job is extremely interesting.” Cas chimes in. Sam raises an eyebrow because he hasn’t heard that one before. Dean owned a small mechanic and car restoration shop. His brother loves his business, Sam is proud as hell of his brother, but other people tend to look down on the work. 

“That’s only because I was the only one that would take a look at your ugly-ass pimp mobile.” Dean says with a fond roll of his eyes. 

Jo briefly interrupts them to take their orders. Sam and Dean order their usual of garden salad and bacon cheese burger. Cas orders a peanut butter burger with sweet potato fries, this also makes Sam raise an eyebrow. Who actually orders the PB Burger?

“You fixed his car?” Sam asks, internally shrugging off the weird food order. “Is that how you met?”

“Yeah, Cas’ car was a total wreck and apparently he had been turned down by every other mechanic in town.” Dean explains. 

“I don’t know why.” Grumbles Cas. 

“‘Cause the entire engine was being held together with duct tape!” Dean throws his hands up, this was apparently a well worn argument because both men have a grossly adoring look in their eyes. “I wasn’t even gonna fix it until I saw the owner was insanely hot.” 

“My selfless hero.” Cas rolls his eyes. 

“Shut up,” Dean says with a giddy smile. “Then he kept coming back with magically broken things or strange noises that didn’t exist just so he could talk to me.”

“You are the owner, you did not need to personally check my car’s functionality every time I came in.” Cas said with another fond roll of his eyes. 

“What can I say, my costumer service is five stars.” Dean gives a cheeky grin. 

“So, Cas,” Sam breaks in because as endearing as their banter is, he has an investigation to continue, “what’re your hobbies?” 

Dean rolled his eyes at Sam’s question. He did my say anything though because he knows Sam means well. Sam had added this question to his interrogation after one of his own dates said one of their hobbies were taxidermy and sex. You can learn a lot about a person by how they spent their free time 

“I read, watch documentaries, run, care for my bees, garden, and recently Dean has been introducing me to various pop culture cinema and music.” Okay those all seem normal, except...

“Bees?” 

“Correct.” Cas nods while taking a sip of his beer. “I have a bee hive in my garden. They are unimaginably fascinating and beneficial to our planet and society. To produce a mere pound of honey it takes them 90,000 miles, or three times around the earth. This is rather impressive as they fly about six miles an hour...” Cas trails off as he seems to realize his ranting.

“I’ve summed it up to Cas really likes bees.” Dean provides just as their food comes. “It’s adorable though.” Now both Cas and Dean are blushing like crazy, oh god. 

The rest of the meal goes by quickly. Sam learns more about his brother’s boyfriend and they have a nice conversation about a book Sam has recently read. 

By the time their burgers was finished and pie was eaten -Dean SHARED his piece with Cas who wanted to taste both pecan and apple- Sam has decided he likes Cas. He really likes Cas. 

Throughout the meal he had seen Dean’s dopey grins and heart eyes. He had seen Cas gently reprimand his brother when he made self deprecating comments. He saw Dean patiently explain any and every pop culture reference to Cas who had his head tilted and eyes squinted. 

So when Dean asks him what he thinks after Cas had excused himself to the bathroom in the middle of pie, Sam smiles and says he’s great. He watches his brother’s eyes light up impossibly brighter. 

“I think I might love him, Sammy.” Dean almost whispers. 

“You think?” Sam asks with a raised eye brow, because from where Sam is sitting is older brother is head over heals whipped for the guy. 

Years later when Sam is his brother’s best man at Dean and Cas’ wedding he’ll tell the story of meeting Dean’s husband. He’ll describe how Cas had come in a whirl wind of awkwardness in a trench coat and had a rant about bees. For now, he’ll enjoy the soft look of his brother falling in love.


End file.
